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This story is from a few years ago, but I thought I might share -- I'd love to find another Lily to share an experience like this
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I looked into her enchanting hazel eyes and paused. “Are you sure?” I managed again after I found my voice.
Lily looked back at me, “Yes, come with me” she whispered as she led me by the hand down the long hallway back to her bedroom.
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In the Spring, I moved from my childhood home in the Midwest to the heart of Atlanta, Georgia. This move was a fresh start. I was moving to a new state, new friends, and a new job and leaving behind both the joys of long old friends and the pain from a far too long bad relationship.
The move had been sudden. When I found my new job, they asked me to start quickly, and I reached out to an old friend -- who now lived in Atlanta, for advice on where I should live. The advice came quickly and I found myself living in a loft in Midtown. A location both near Georgia Tech and very close to my new job.
I quickly learned that my friend’s advice, had been as much about using me as her guinea pig as it was about being helpful. While the location turned out to be fantastic; it was an apartment complex she was interested in moving into and wanted to find out if it was a good place to live before doing so. In her judgement, it was a good complex, and soon she moved into the complex along with her “best friend in the world” and roommate, Lily.
Over the course of the Summer, I spent my evenings and weekends with the two roommates constantly and grew quite close to them both and to Lily in particular. Lily was a short spunky blonde with a firecracker personality and a heart for adventure. She was also very attractive. At just over five feet tall -- or five feet one inches as she insisted -- she had long flowing blonde hair and mesmerizing hazel eyes. You could stare into her eyes and lose yourself; the shade and complexion changing based on her mood. More than once I found myself starting to get lost in those eyes, only for her to look up and ask me what I could be staring at. I also, a little guiltily, noted her womanly body and admired her thin frame, firm double D cup breasts, and the pert curve of her butt. I loved to watch her walking away.
As the Summer came to a close, Lily's roommate began her “big girl job” and traveled constantly. She was on the road most weeknights and Lily and I grew closer and closer -- perhaps a little to the jealousy of her roommate. Many nights, Lily would come to my apartment, and I would cook a fancy dinner for her, we would enjoy a bottle or two of wine, and relax while watching South Park, her favorite show. I found myself increasingly attracted to Lily, but worked hard to suppress those feelings as she was extremely loyal to her longterm boyfriend. Finally, one night, after a dinner party I threw for both Lily and her roommate and both girl’s boyfriends -- it changed. She told her boyfriend it was over and was ready to make a fresh start.
Over the coming weeks, we spent more and more time together. Both of us growing closer but also recognizing the loss she’d had and not wanting to rush anything. One Saturday afternoon, we sat in her apartment, having just finished a light lunch, sharing a bottle of wine. We both felt a little loopy, but were just relaxed and enjoying life together. As we sat in her living room, the subject of conversation turned to sex.
“You know”, she stated, looking deep into my eyes, her cheeks flushed a little from embarrassment and a little from the wine. “It’s been years since I’ve had an orgasm.”
I looked at the small blonde vixen in front of me in disbelief. “There’s no way that can be” I questioned. “Surely, for as long as you dated Jason and for the number of times you let him stay over with you, he must have pleased you?”
“No, never” she replied. “Given his religious beliefs, there were times he would let me please him”, she paused, “and then make us both feel guilty about it. But never was there a time that he pleased me. It was always something he made me feel guilty about. My inability to orgasm from anything he would do to me.”
We both looked into each other's eyes. Our skin a little flushed, feeling emotions we both worked to suppress working their way slowly to the surface.
“In fact,” she continued, “the last person to give me an orgasm was actually an old roommate of his.”
I looked, with disbelief, at the new naughty side I was seeing from this innocent young college girl.
“There was a night,” she shared, “before we started dating, that I spent with his roommate.” She blushed visibly now. “I came so hard that night. He knew how to please me.” She looked away as she finished her statement and giggled nervously.
“Surely, Lily, you touch yourself and bring yourself to orgasm?” I asked. Surely this beautiful girl, with this newly revealed naughty side, at least found pleasure from herself when she wanted it.
“No!” She looked at me shocked. “Why would I do that, it would be so naughty! Besides, I’m a virgin!”
I looked back at her, realizing it had literally been years since she was fulfilled sexually. I paused for a moment, realizing she was a complex mixture of naughtiness and innocence. I felt conflicting emotions rise -- both a desire to protect her and a desire to explore her naughty side with her further.
“I just can’t believe he never pleased you.” I responded, working to again make eye contact with those beautiful eyes. “I mean, when I’ve had a girlfriend, pleasing her is a huge part of that aspect of our relationship. In fact, I can’t tell you how aroused it makes me to see the pleasure I can bring to her.”
Lily looked up into my eyes as I stood to refill our glasses. I struggled to hide the growing stiffness in my jeans as I walked over to the bottle and poured generously for us both. “Do you really mean that?” she asked?
“Of course!” I responded emphatically. “I very much enjoy bringing pleasure to my partner, and couldn’t imagine a relationship as one sided as the one you describe.” I paused for a moment. “I also can’t imagine not being able to bring my partner to orgasm -- it’s just never been a problem for me.”
I brought the glasses back to the couch and sat down next to her -- closer this time. Not wanting to push too fast or to take advantage of her potentially vulnerable emotional state, following her breakup, but feeling my emotions for her growing and my desire for her surging with this conversation.
I started to sip my wine when I heard her softly ask “How?”
I almost choked. “What?” I managed to rasp in response.
“How? How is it that you are so confident you would be able to please a woman?”
I took a long, slow, drink from my glass, working to gather my composure. This innocent, young, friend of mine was asking how I was so confident I could give a woman an orgasm. I couldn’t help but wonder where this was going, but also tried to consider where she was and not wanting to lead her to do something she might regret and that would hurt the friendship we’d built. I also considered how she might react to my answer -- would it change the way that she saw me?
I looked back up into her questioning eyes. “I’m actually quite good at kissing and using my mouth to please a woman.” I said slowly.
She looked back at me curiously. “You mean, you can give an orgasm, just from kissing?”
I smiled a little, “Well, yes from kissing, but specifically from kissing down there.” I indicated, glancing down toward her firm thighs.
Lily blushed a little and looked away for a moment before returning to look into my eyes. “But isn’t that dirty?” she almost whispered.
I looked into her eyes, my desire for her growing; I smiled at her innocence. “It could be seen that way, but I find it anything but.” I paused, but decided we’d come this far and there was no sense stopping now. “I actually really enjoy the taste of an aroused woman down there. I love the feel of her lips against my tongue and my kisses. I can’t even describe how turned on I get from the sexy scent of her arousal when I get to kiss her. I’ve even cum, without anyone touching me, just from how aroused I am from going down, Lily.”
I sipped my wine as I saw her start to sip a little more liberally. She blushed deeply as I continued. “I find it so intimate to kiss a woman in such a private place. I love to kiss up and down her thighs, smelling her become wetter and wetter, her arousal growing, until she pulls my face toward her to please her. I love feeling a woman’s legs lift over my shoulders to open herself more for me and feeling her run her hands through my hair and grinding her lips against my kisses as she cums hard.”
I lifted my eyes once again to meet her gaze. She was looking back into my eyes, her mouth open slightly. I could see her taking deep breaths and the flush of her cheeks. I’m sure I was giving her a similar sight -- a mixture of repressed desire, both of us wanting to avoid endangering our friendship, with a lowering of inhibitions, both of us wanting to jump in and go further.
As we stared quietly at each other I heard her whisper “show me”.
“Are you sure?” I questioned. Suddenly, the reality of the situation hitting me. I remembered a few days earlier, the passionate kissing we did, embracing and rolling from her couch to the floor. Holding her small frame in my arms, kissing her lips hungrily, just to hear a key in the door and us both struggling to break apart and compose ourselves as her roommate let herself in. Where was her roommate now? Would she come back in the middle of this? Would Lily be loud as I pleased her and would her roommate hear us? What would my old friend think if she found me with my head buried between her best friend’s legs -- a girl I wasn’t even dating, dragging my tongue through her lips as she squirmed and moaned in pleasure. What would Lily think? Would she regret this once we both stepped away from the moment? Once we both sobered up? I wanted, so badly to show her, but would I be ruining a relationship that I hoped to see turn into so much more?
“Show me!” she repeated insistently.
I looked into her enchanting hazel eyes and paused. “Are you sure?” I managed again after I found my voice.
Lily looked back at me, “Yes, come with me” she whispered as she led me by the hand down the long hallway back to her bedroom.
I watched her beautiful firm little butt as she walked down that hallway, following her as if I were in a trance. We entered her bedroom and she shut the door. All the echos from the large open concrete room shrinking as we entered this smaller cozier space. She stood before me, in her socks, a pair of short white shorts, and a polo. I wondered, not for the first time, what kind of panties she might be wearing, and realized that I was about to find out. I reached forward and brushed her long hair behind her ears, kissing her softly on the lips.
She smiled up into my eyes as I felt her unbuckle my belt, unsnap my jeans, and push them to the ground. I felt thankful I wore a pair of black silk boxers that day, and felt my growing length continue to stiffen as my jeans hit the floor. As I stepped out of my jeans, Lily turned and crawled slowly onto her bed, her cute little butt wiggling as she crawled from the foot to the head, then flipped over, her head on the pillows waiting for me to join her.
I kicked off my socks and slipped out of my t-shirt. Standing there in only my tented black silk boxers, then crawling up the length of the bed to join her. I lay beside her on the bed, kissing her softly and letting my hands gently trace along the curves of her body. I avoided the swell of her breasts, not wanting to scare her away, as I gently felt her soft skin and pulled her closer to me.
As I felt our soft kisses grow more intense, I let one hand slip to the top of her shorts, then gently pulled her shirt up her firm stomach, feeling the soft skin under my fingers as I gently sucked her tender little tongue into my kiss. I broke our kiss slowly, sucking gently on her bottom lip, and looking into her eyes I lowered my kiss to her firm stomach. I held eye contact with her as I slowly trailed my kisses down her firm stomach, her legs spread on either side of my body as I kissed lower and lower along that soft flesh. I smiled up at her as I flicked the tip of my tongue gently through her belly button, tracing gently in a circle along the edge, thinking of how I would soon be doing something very similar for her hard little clit.
I smiled up at her as I leaned up and knelt on her bed so that I could kiss each of her knees, then gently, slowly started kissing back and forth along her legs, tracing my kisses up her thighs to the bottom of her shorts. I held her gaze as I traced my tongue gently along the edge of her shorts, where they met her thighs, and reached under her to cup her little butt in my hands.
She growled softly in frustration and reached down to unbutton and push off her shorts. This girl knew what she wanted! I looked up at her soft yellow lace panties, smiling as I caught a whiff of her sweet scent and could see the fine wisps of hair peeking out from beneath.
Lily started to reach to push down her panties, but I gently pushed her hands back as I leaned in and buried my nose in her panties, feeling her fleshy lips spread to either side. I moaned loudly at her scent, and kissed her damp panties gently. She groaned loudly, feeling my hot breath against her wet skin as I kissed and sucked her lips through her panties while rubbing her little clit with my nose.
I looked up into her eyes as I kissed her inner most thighs, sucking on the tender skin between her thighs and her lips. Her head was back on the pillow as her chest heaved softly. I kissed along the edge of her panties on each side, dipping my tongue under now and again to taste the skin beneath.
I kissed my way up over her soft panties, loving the musky sweet scent of her arousal as I felt the top of her panties brush over my lips. I smiled as I took the soft fabric between my lips and gently lowered my head, pulling them down her body. I smiled as I could see the red swollen lips beneath, her wispy pubes emphasizing the untouched virgin flesh I was exploring. I pulled them down a little further and began to tease her growing clit with the tip of my nose, letting it brush the little nub briefly back and forth. She moaned loudly and I felt her legs jerk with each brush.
Finally, I reached down and pulled her sexy panties from her body, leaning in slowly to plant gentle kisses along her red swollen lips. Watching her squirm for more as I teased her and took my time enjoying the soft sweet taste of her virgin pussy.
Once again, I looked up into her eyes and extended my tongue, curling the tip to lick from deep between her legs, dragging the rough flesh up over her hard little clit. She gasped in pleasure, jerking first from the feel of my tongue, and then from the pressure on her clit. I moaned -- I love the sweet tangy taste of a woman's pussy, and this pussy was so sweet. I think knowing it was innocent and I was the first to taste her made it even better.
I felt her hand reach back and take my head to guide me back to her clit. I smiled, she's a fast learner. I kissed her little clit gently at first, then kissing it more deeply and sucking it into my kisses. She began to writhe under me and I reached one hand to cup her butt and feel her tensing it as she squirmed and moaned.
I kept kissing and sucking her little clit, feeling her spreading her legs even further for me. I smiled as I began to flick her little clit with my tongue each time I pulled it into a deep kiss. It was too much for her and she thrashed back onto the bed. I kept kissing and licking and flicking as she shook and screamed. Finally, as she started to come down, I placed gently kisses along each of her pussy lips until she pushed my head away.
I lay down on the pillow next to her and looked into her satisfied half-closed eyes. She looked at me -- "that was amazing, I've never felt anything like that!" I leaned in for a kiss, and the moment broke -- she jerked away. "What are you doing? Do you know where that mouth has been?"
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